3-Amino-1-propanol → 4-[(3-Hydroxypropyl)amino]-3-nitrobenzonitrile

HRID 590382Notes

Reaction equation

HRID 590382 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH2:13][CH2:14][CH2:15][CH2:16][OH:17].C(N(C(C)C)CC)(C)C>C1COCC1>[OH:17][CH2:16][CH2:15][CH2:14][NH:13][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 27746544-Fluoro-3-nitrobenzonitrile

Product 1

HCID 223493164-[(3-Hydroxypropyl)amino]-3-nitrobenzonitrileYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-fluoro-3-nitrobenzonitrile (1.0 g; 6.02 mmol), 0.502 ml (6.62 mmol) of 3-amino-propan-1-ol and 1.15 ml (6.62 mmol) of diisopropylethylamine in 5 ml THF is stirred at rt for 1 hr (temperature raises somewhat at the beginning). After concentration in vacuo the residue is dissolved in 50 ml of ethyl acetate, washed with 50 ml of 4% aqueous sodium hydrogen carbonate and brine, dried and concentrated. 1.32 g of pure title compound as a solid are thus obtained (99% yield).

Workup

  1. temperatureraises somewhat at the beginning)
  2. concentrationAfter concentration in vacuo the residue
  3. dissolutionis dissolved in 50 ml of ethyl acetate
  4. washwashed with 50 ml of 4% aqueous sodium hydrogen carbonate and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5d0c142ce289451f80b92e96fccac0b6
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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